Why I’m Playing Daily Fantasy Sports in 2025. And Why You Should Too
More and more frequently, I’m asked what Daily Fantasy Sports is — and why I’ve stuck with it for more than a decade. Fans today have more ways than ever to get invested in the games they love. Season-long drafts (and the punishments from last year’s standings) are wrapping up or scheduled soon. Best Ball drafts are streaming endlessly. Sports betting has been gaining momentum for years, and Pick’em games continue their popularity. Even prediction markets are creeping onto the horizon with their definitely-not-sports-betting-in-any-way products.
Some younger bettors may not even realize that FanDuel and DraftKings offer more than just sports betting. But in December 2014, I took the winnings from my home fantasy football leagues and deposited them to start playing a different option — Daily Fantasy Sports (DFS). Ten years later, I’ve earned more than $4 million in profit. DFS has changed my life. Here’s why I’m still playing in 2025, and why I think you should, too.
You can win money. A lot of money. And then you can keep winning money.
My first big win came on May 23, 2016. I had played DFS nearly every day in 2015 and managed a small profit, but it was up and down to say the least. On that Monday night in 2016, though, everything changed. Stephen Vogt hit a home run in the late West Coast game, adding just enough points to push my lineup into first place — while also securing the win bonus for my pitcher, Rich Hill. I woke my wife up to tell her we were suddenly $50,000 richer. We could pay off a big chunk of my student loans and even afford a real vacation.
The wins grew slowly but steadily after that. My hometown Nationals played the Rockies in Coors Field on April 25, 2017, in a game with a sketchy weather forecast. On the advice of a trusted sports meteorologist, I stacked the game with confidence. After a long, rain-delayed night, I walked away $100,000 richer and with the unbelievable feeling that I had just won six figures at fantasy sports.
More than a year later, on August 18, 2018, I attended my first live final — the FanDuel World Fantasy Baseball Championship. With four of the 100 entries, I brought some of my closest friends across the country to San Diego to watch me compete. One of my entries finished dead last, earning me some good-natured ribbing from my friends. But another entry finished in first place, adding $300,000 to my bankroll and earning me my first live final trophy.
The momentum carried forward. On April 24, 2021, in the middle of the COVID era, I notched a second live final win — this one from my living room couch. With four entries in the FanDuel World Fantasy Basketball Championship, I finished both first and second for a $700,000 payday. Then came the biggest score of my career: September 18, 2023. On a Monday night that saw Browns RB Nick Chubb go down with a brutal injury, I rode backup Jerome Ford to a solo $1 million win in the DraftKings Milly Maker. And just this year, I finally claimed a DraftKings live final title with a first-place finish at the Fantasy MMA World Championship 2025 Live Final in June.
I’m not listing out these wins to claim I’m the best fantasy sports player in the world. I know I’m not. Plenty of other players have either won more or won more consistently. But my results have still changed my life — and they prove something important.
If you walk into a casino and win every hand of poker, the casino doesn’t kick you out; they put your name on the sign outside to attract more players. The casino still makes money off the rake. But if you walk into a casino and win every hand of blackjack — or walk into a sportsbook and beat the house every night — that conversation goes very differently. You’re taking money directly from the house, and the house doesn’t like losing. Even if you can find a way to become successful at sports betting, you will soon find yourself limited by the books and looking for ways just to get bets down.
That’s the advantage of DFS. Not only can you win, but you can win big and then keep winning.
Your favorite team stinks. And your same-game parlay isn’t sending you a championship belt - even if it hits.
As a kid in the late 80s, I made a regrettable decision. It had nothing to do with getting a perm or a high-top fade. Even worse, I chose to become a fan of the Washington Bullets, my hometown basketball team. I knew the team was bad, but I felt that if I kept rooting for the home team, the championships would be that much sweeter when they came.
Nearly forty years later, I’m still waiting for the Bullets/Wizards to even put together a competitive team. A disproportionate number of successful fantasy players are Wizards fans — forged by years of mediocrity, we realized that if we were ever going to win a championship, we’d have to do it ourselves. With leagues adding more franchises every few years, it’s a sobering reality that some fans may spend their entire lives rooting for their team without ever seeing a conference finals.
With DFS, every slate is a chance to chase a title — whether it’s a nightly win, a big tournament score, or a live final with a literal belt on the line. That FanDuel championship in 2018 felt like winning a World Series ring. I didn’t care that the Wizards were still floundering. I had my own trophy, my own banner moment, earned with my own decisions. That’s something your same-game parlay just can’t give you.
And speaking of parlays, you may want to check the rake. According to ESPN, in some states, sportsbooks have reported holding upward of 20–30% of the amount wagered on parlays. Rake for DFS contests generally tops out at 16%, with some contests dipping into the single digits. The math alone is another reason DFS gives you a better shot.
You can win over a reasonable timeframe
There’s no denying that Best Ball drafts are fun. They capture the best part of the season-long experience at a reduced commitment during the season. But if you draft in August and get paid out in January, you’re waiting six months for your money. A 6-month CD is paying 4.5% APY right now. That doesn’t come with the excitement of Best Ball, but it’s not nothing — and at least you don’t have to pray your one of your tight ends is still walking in December for the payout.
On the other end of the spectrum, live betting games on a sportsbook app can get you an immediate payout, but how often does that last? Putting your 25% odds boost on whether a team gets a first down and winning can feel great. But doubling down on the next drive can leave you with a sinking feeling before the night is over.
The “Daily” in Daily Fantasy Sports strikes a balance. You know what you’re in for. If you’ve got an edge, you can apply it again tomorrow, and the next day, and the next. You don’t have to wait until next year’s contests to compound your edge.
You play against other people, and that’s meaningful
At the end of the day, DFS isn’t about beating the house — it’s about beating other players. This is why many of us started playing fantasy sports to begin with. We keep in touch with our old colleagues and classmates by creating fake teams named after our favorite players or our beloved, and draft real players to compete against each other. This is primarily an American pastime, where we put aside our political differences for a moment to try to outmaneuver our friends, with the loser often condemned to an embarrassing but recoverable fate.
In the DFS version of fantasy sports, that distinction may be more subtle, but over the years, I have come to value the difference more and more. People I’ve gotten into bitter online arguments with have become people I look forward to seeing at live final events. My daughter has practically grown up at live finals, flying around the country in a small “Squirrel Patrol” jersey, cheering and watching the games, and asking me which team on TV is the Squirrel Patrols. We are real people competing against other real people, and that makes a difference.
I’m not knocking season-long leagues, Best Ball drafts, or even sports betting — they all have their place and their appeal. But DFS offers something sportsbooks and season-long leagues can’t: the ability to win, to keep winning, and to do it against real people who are chasing the same dream. That’s why I’m still playing Daily Fantasy Sports in 2025 — and why you should, too.
Come join us at 4for4
I hope you’ll join us at 4for4 this season with our DFS plan. You’ll get access to my weekly write-ups and picks for the main NFL slate, along with Thursday Night Football and Monday Night Football, as well as our subscribers-only Discord channel (where I’ll be on Sunday mornings), weekly podcasts, cash game recommendations, and additional primetime slate write-ups. The time to join is now – our DFS plan comes with all of the benefits of our excellent season-long package, meaning you can get the best preparation for your upcoming drafts and add the DFS plan for less than $20 more with the code below.
- 📝 Sign up: https://4for4.com/plans
- 🎟️ Choose the DFS plan
- 💸 Use code SQUIRREL for 25% off the $99 season sub
